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Abstract

The title compound, C15H12O2S, was prepared by the oxidation of 3-methyl­sulfanyl-2-phenyl-1-benzofuran with 3-chloro­peroxy­benzoic acid. The phenyl ring makes a dihedral angle of 37.65 (8)° with the plane of the benzofuran fragment. The O atom and the methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by aromatic π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.549 (2) Å] and by inter­molecular C—HO inter­actions.

Related literature

For the crystal structures of similar 3-methyl­sulfinyl-2-phenyl-1-benzofuran compounds, see: Choi et al. (2007a,b).

supplementary crystallographic
information

Comment

This work is related to our previous communications on the synthesis and
structure of 3-methylsulfinyl-2-phenyl-1-benzofuran analogues, viz.
5-chloro-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al.,
2007a) and 5-methyl-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi
et
al., 2007b). Here we report the crystal structure of
3-methylsulfinyl-2-phenyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.009 (2) Å from the least-squares plane defined by the nine constituent atoms. The
phenyl ring (C9—C14) makes a dihedral angle of 37.65 (8)° with the plane of
the benzofuran fragment. The molecular packing (Fig. 2) is stabilized by
aromatic π—π stacking interactions between the benzene rings from the
adjacent molecules. The Cg···Cgii distance is 3.549 (2) Å
(Cg is the centroid of C2—C7 benzene ring, symmetry code as in Fig.
2). The crystal structure is further stabilized by C—H···O (Fig. 2)
interactions between a methyl H atom and the oxygen of the S=O unit, with a
C15—H15C···O2i separation of 2.36 Å (Fig. 2 and Table 1; symmetry code
as in Fig. 2).

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.